Bromine → HCID 136152308, compound

HRID 1459173Notes

Reaction equation

HRID 1459173 reaction equation
[Br:1]Br.[CH2:3]([O:5][P:6]([CH2:11][O:12][CH2:13][CH2:14][N:15]1[CH:23]=[N:22][C:21]2[C:20](=[O:24])[NH:19][C:18]([NH2:25])=[N:17][C:16]1=2)([O:8][CH2:9][CH3:10])=[O:7])[CH3:4]>O>[Br:1][C:23]1[N:15]([CH2:14][CH2:13][O:12][CH2:11][P:6]([O:5][CH2:3][CH3:4])([O:8][CH2:9][CH3:10])=[O:7])[C:16]2[N:17]=[C:18]([NH2:25])[NH:19][C:20](=[O:24])[C:21]=2[N:22]=1

Participants

4

Reactant 2

HCID 24408Bromine4×HCID 135404759HCID 135404759, compound

Product 1

HCID 136152308HCID 136152308, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Bromine (1 mL) was added to 100 mL of water and the mixture stirred vigorously at rt until all the bromine had dissolved (15 min.). 9-(2'-(diethylphosphonomethoxy)ethyl)guanine (0.360 g, 1.04 mmol) was then dissolved in 10 ml H2O and treated dropwise with the aqueous bromine solution until the color of Br2 persisted. The reaction mixture was allowed to stand at 0° C. for 1 h and then was concentrated to afford a dark yellow viscous gum. Purification was accomplished by column chromatography on silica gel (MeOH--CH2Cl2) to provide 0.31 g of 8-bromo-9-(2'-(diethylphosphonomethoxy)ethyl)guanine as an orange powder.

Workup

  1. dissolutionhad dissolved (15 min.)
  2. concentrationwas concentrated
  3. customto afford a dark yellow viscous gum
  4. customPurification

Sources & evidence

ORD record
ord-f59f2a2a4cfa4ace9895215e7e54f74f
Source dataset
uspto-grants-1998_12
Patent number
US05854228

Reaction notes

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